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United States Patent (19) 11 Patent Number: 5,929,295

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United States Patent (19) 11 Patent Number: 5,929,295 USOO5929295A United States Patent (19) 11 Patent Number: 5,929,295 Wu et al. (45) Date of Patent: Jul. 27,9 1999 54 HYDRODEALKYLATION AND 5,234,872 8/1993 Apelian et al. ........................... 502/62 TRANSALKYLATION OF C+AROMATIC 5,242,676 9/1993 Apelian et al. 423/714 COMPOUNDS 5,378,671 1/1995 Keville et al. ............................ 502/64 5,406,016 4/1995 Cook et al. ............................. 585/475 75 Inventors: An-hsiang Wu; Ralph J. Melton, both 5,500,1092- Y-Y-2 3/1996 Keville et al. .......................... 208/111 of Bartlesville; Charles A. Drake, 5,506,182 4/1996 Yamagishi et al. ....................... 502/66 Nowata, all of Okla. FOREIGN PATENT DOCUMENTS 73 Assignee: Phillips Petroleum Company, 1343172 1/1974 United Kingdom .............. CO7C 3/58 Bartlesville, Okla. Primary Examiner-Glenn Caldarola Assistant Examiner Thuan D. Dang 21 Appl.App No.: 08/907,1949 Attorney,y, AgAgent, or Firm-Lucas K. Sha y 22 Filed: Aug. 6, 1997 57 ABSTRACT 51 Int. Cl. ................................. C07C 5/22; CO7C 4/12 A catalyst composition, a proceSS for producing the com 52 U.S. Cl. .......................... 585/475; 585/489; 585/488; position and a hydrocarbon conversion proceSS for convert 585/485; 585/486 ing a Co+ aromatic compound to a C to Cs aromatic 58 Field of Search ..................................... 585/475, 489, hydrocarbon Such as a Xylene are disclosed. The composi 585/485, 488, 486; 502/202, 206, 208, tion comprises an acid-treated Zeolite having impregnated 211, 232, 302,303, 304,305, 306, 309, thereon a metal or metal oxide. The composition can be 310,340, 350, 352, 344, 355 produced by incorporating the metal or metal oxide into the Zeolite. The hydrocarbon conversion process comprises con 56) References Cited tacting a fluid which comprises a Co+ aromatic compound with the catalyst composition under a condition Sufficient to U.S. PATENT DOCUMENTS effect the conversion of a Co+ aromatic compound to a C 4,582,815 4/1986 Bowes ....................................... 502/64 to Cs aromatic hydrocarbon. 5,200,158 4/1993 Apelian et al. ... 423/714 5,202,516 4/1993 Lee et al. ................................ 585/467 18 Claims, No Drawings 5,929.295 1 2 HYDRODEALKYLATION AND catalyst in a hydrocarbon conversion is provided. The pro TRANSALKYLATION OF C+AROMATIC cess can comprise (1) optionally calcining a Zeolite to COMPOUNDS produce a calcined Zeolite; (2) contacting a Zeolite or a calcined Zeolite with an acid under a condition Sufficient to FIELD OF THE INVENTION produce an acid-treated Zeolite; (3) contacting the acid This invention relates to a catalyst composition useful for treated Zeolite with an activity promoter precursor Selected converting a Co+ aromatic compound to a C to Cs aromatic from the group consisting of Silicon compounds, phosphorus hydrocarbon, to a proceSS for producing the composition and compounds, boron compounds, magnesium compounds, tin to a proceSS for using the composition in a hydrodealkyla compounds, titanium compounds, Zirconium compounds, tion process. molybdenum compounds, germanium compounds, indium compounds, lanthanum compounds, cesium compounds, BACKGROUND OF THE INVENTION and combinations of two or more thereof under a condition It is well known to those skilled in the art that aromatic Sufficient to incorporate the activity promoter into the Zeolite hydrocarbons are a class of very important industrial chemi to form a modified Zeolite; and (4) calcining the modified cals which find a variety of uses in petrochemical industry. 15 Zeolite. Recent efforts to convert gasoline to more valuable petro According to a third embodiment of the present invention, chemical products have therefore focused on the aromati a process which can be used for converting a Co+ aromatic Zation of gasoline to aromatic hydrocarbons by catalytic compound to a C to Cs aromatics compound is provided cracking in the presence of a catalyst. The aromatic hydro which comprises, consists essentially of, or consists of, carbons produced by the aromatization process include C to contacting a fluid which comprises a Co+ aromatic Cs hydrocarbons Such as benzene, toluene and Xylenes compound, optionally in the presence of an inert fluid Such (hereinafter collectively referred to as BTX) which can be as a hydrogen-containing fluid, with a catalyst composition, useful feedstocks for producing various organic compounds which is the same as disclosed above in the first embodiment and polymers. However, heavier, leSS useful aromatic com of the invention, under a condition effective to convert a Co+ pounds are also produced during the aromatization process. 25 aromatic compound to an aromatic hydrocarbon containing It is, therefore, highly desirable to convert these compounds 6 to 8 carbon atoms per molecule. to the more useful BTX. DETAILED DESCRIPTION OF THE Though a number of catalysts have been used in a INVENTION hydrodealkylation or transalkylation process, the conversion According to the first embodiment of the invention, a of a C+ aromatic compound and the Selectivity to BTX are composition which can be used as catalyst in a transalky generally not as high as one skilled in the art would desire. lation or hydrodealkylation process for converting a C+ Furthermore, a catalyst used in the hydrodealkylation or aromatic compound to a C to Cs aromatic hydrocarbon is transalkylation of these heavier aromatic compounds is provided. The composition comprises, consists essentially generally deactivated in a rather short period because of 35 of, or consists of, a Zeolite having incorporated therein, depositions of carbonaceous material Such as, for example, preferably impregnated thereon, an activity promoter coke on the Surface of the catalyst. Selected from the group consisting of Silicon, phosphorus, Accordingly, there is an ever-increasing need to develop boron, magnesium, tin, titanium, Zirconium, molybdenum, a catalyst and a proceSS for converting these heavier and leSS germanium, indium, lanthanum, cesium, any oxide thereof, useful aromatic compounds (mainly trimethyl- and 40 and combinations of two or more thereof wherein the tetramethylbenzenes) to the more valuable BTX hydrocar activity promoter is present in the composition in a coke bons while Simultaneously Suppressing the coke formation. Suppressing amount, or an activity-enhancing amount to Such development would also be a Significant contribution improve the conversion of a Co+ aromatic compound, when to the art and to the economy. the composition is used in a transalkylation process. 45 According to the first embodiment of the invention, the SUMMARY OF THE INVENTION weight ratio of the activity promoter to the acid-treated An object of this invention is to provide a catalyst Zeolite can be any ratio So long as the ratio can enhance or composition which can be used to convert a C+ aromatic improve the conversion of a Co+ aromatic compound or compound to a C to Cs aromatic hydrocarbon. Also an SuppreSS or reduce the formation or deposition of coke on a object of this invention is to provide a proceSS for producing 50 Zeolite catalyst during the transalkylation process for con the catalyst composition. Another object of this invention is verting a C+ aromatic compound to a C to C aromatic to provide a proceSS which can employ the catalyst compo hydrocarbon. Generally, the ratio can be in the range of from Sition to convert Co+ aromatic compounds to C to Cs about 0.0001:1 to about 1:1, preferably about 0.0005:1 to aromatic compounds. An advantage of the catalyst compo about 1:1, more preferably about 0.001:1 to about 0.8:1 and Sition is that it decreases coke deposits thereon and exhibits 55 most preferably from 0.005:1 to 0.5:1 for effective hydro high transalkylation activity, Satisfactory yield of Xylenes carbon conversion and coke reduction or Suppression. and BTX and good stability. Other objects and advantages Alternatively, the activity promoter can be present in the will become more apparent as this invention is more filly catalyst composition in the range of from about 0.01 to about disclosed hereinbelow. 50, preferably about 0.05 to about 50, more preferably about According to a first embodiment of the present invention, 60 0.1 to about 45, and most preferably 0.5 to 33 grams per 100 a composition which can be used as a catalyst for converting grams of the catalyst composition. The term “acid-treated a Co+ aromatic compound to a C to Cs aromatic hydrocar Zeolite” refers to a zeolite which has been contacted with an bon is provided. The composition can comprise an acid acid, as described in the Second embodiment of the treated Zeolite having incorporated therein an activity pro invention, before the Zeolite is incorported with an activity moter. 65 promoter. According to a Second embodiment of the invention, a If a combination of two or more activity promoters is proceSS for producing a composition which can be used as employed, the atomic ratio of one promoter to other 5,929.295 3 4 promoter(s) can be in the range of about 0.01:1 to about C. for about 0.5 to about 50 hours, preferably about 1 to 10:1, preferably about 0.1:1 to about 8:1, more preferably about 30 hours, and most preferably 1 to 20 hours, prefer about 0.5:1 to about 5:1, and most preferably 1:1 to 3:1. The ably under atmospheric pressure. Thereafter, the dried, presently preferred composition is an acid-treated beta Zeo Zeolite-binder mixture can be further calcined, if desired, in lite having impregnated thereon molybdenum or molybde air at a temperature in the range of from about 300 to 1000 num oxide. C., preferably about 350 to about 750 C., and most pref erably 450 to 650° C. for about 1 to about 30 hours to According to the present invention, any activity promoter prepare a calcined Zeolite-binder.
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